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Identification
YMDB IDYMDB00656
NameD-glucitol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSorbitol (glucitol) is a six-carbon sugar alcohol found in apples, pears, peaches, and prunes. It is synthesized by sorbitol-6-phosphate dehydrogenase, and converted to fructose by succinate dehydrogenase and sorbitol dehydrogenase. Succinate dehydrogenase is an enzyme complex that participates in the citric acid cycle.
Structure
Thumb
Synonyms
  • (-)-Sorbitol
  • (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
  • 1,2,3,4,5,6-Hexanehexol
  • Cholaxine
  • clucitol
  • Cystosol
  • D-(-)-Sorbitol
  • D-1,2,3,4,5,6-hexanehexol
  • d-Galactitol
  • D-Glucitol
  • d-sorbit
  • d-Sorbite
  • D-Sorbitol
  • D-Sorbol
  • Diakarmon
  • Esasorb
  • Glucarine
  • glucitol
  • Glucitol, D-
  • gulitol
  • Hexahydric alcohol
  • Hexitol
  • Karion
  • l-gulitol
  • Multitol
  • Nivitin
  • Orbit
  • Probilagol
  • Resulax
  • Sionit
  • Sionit K
  • Sionite
  • Sionon
  • Siosan
  • Sorban
  • Sorbelite C
  • Sorbicolan
  • Sorbilande
  • Sorbilax
  • sorbite
  • Sorbitol
  • Sorbitur
  • Sorbo
  • Sorbol
  • Sorbostryl
  • Sorbostyl
  • Sorvilande
  • e 420
  • e-420
  • e420
  • g-Ol
  • GLC-Ol
  • Sorbitol 3% in plastic container
  • Foodol D 70
  • Karion instant
  • Kyowa powder 50m
  • Neosorb
  • Neosorb 20/60dC
  • Neosorb 70/02
  • Neosorb 70/70
  • Neosorb p 20/60
  • Neosorb p 60
  • Neosorb p 60W
  • Sorbex m
  • Sorbex R
  • Sorbex RP
  • Sorbex S
  • Sorbex X
  • Sorbit
  • Sorbit D 70
  • Sorbit D-powder
  • Sorbit DP
  • Sorbit DP 50
  • Sorbit kyowa powder 50m
  • Sorbit L 70
  • Sorbit S
  • Sorbit T 70
  • Sorbit W 70
  • Sorbit W-powder
  • Sorbit W-powder 50
  • Sorbit WP
  • Sorbitol F
  • Sorbitol FK
  • Sorbitol FP
  • Sorbitol S
  • Sorbitol syrup C
  • Sorbogem 712
  • Medefield brand OF sorbitol
  • Sorbitol pfizer brand
  • Yal
  • Klysma sorbit
  • Medevac
  • Trommsdorff brand OF sorbitol
  • Baxter brand OF sorbitol
  • Pfizer brand OF sorbitol
CAS number50-70-4
WeightAverage: 182.1718
Monoisotopic: 182.07903818
InChI KeyFBPFZTCFMRRESA-JGWLITMVSA-N
InChIInChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
IUPAC Name(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC NameD-sorbitol
Chemical FormulaC6H14O6
SMILESOC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point11 °C
Experimental Properties
PropertyValueReference
Water Solubility2750 mg/mL at 30 oC [MULLIN,JW (1972)]PhysProp
LogP-2.20 [SANGSTER (1994)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m³·mol⁻¹ChemAxon
Polarizability17.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
CaramelFDB030799
OdorlessFDB030799
SweetFDB030799
SMPDB Pathways
Fructose MetabolismPW002390 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
Galactose metabolismec00052 Map00052
SMPDB Reactions
D-glucitol + NADNADH + hydron + keto-D-fructose
KEGG Reactions
NAD + D-glucitolNADH + D-Fructose + hydron
D-Glucose + NADPH + hydronNADP + D-glucitol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Sarthy, A. V., Schopp, C., Idler, K. B. (1994). "Cloning and sequence determination of the gene encoding sorbitol dehydrogenase from Saccharomyces cerevisiae." Gene 140:121-126.8125328
Synthesis Reference:Liu, Haichao; Luo, Chen. Method for manufacturing sorbitol and mannitol with cellulose. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.
External Links:
ResourceLink
CHEBI ID17924
HMDB IDHMDB00247
Pubchem Compound ID5780
Kegg IDC00794
ChemSpider ID24533858
FOODB IDFDB030799
WikipediaSorbitol
BioCyc IDSORBITOL

Enzymes

General function:
Involved in zinc ion binding
Specific function:
L-iditol + NAD(+) = L-sorbose + NADH
Gene Name:
SOR1
Uniprot ID:
P35497
Molecular weight:
38165.39844
Reactions
L-iditol + NAD(+) → L-sorbose + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Reduces the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde similar to GRE2. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation. In pentose-fermenting yeasts, aldose reductase catalyzes the reduction of xylose into xylitol. The purified enzyme catalyzes this reaction, but the inability of S.cerevisiae to grow on xylose as sole carbon source indicates that the physiological function is more likely methylglyoxal reduction
Gene Name:
GRE3
Uniprot ID:
P38715
Molecular weight:
37118.5
Reactions
Alditol + NAD(P)(+) → aldose + NAD(P)H.
(R)-lactaldehyde + NADP(+) → methylglyoxal + NADPH.